Ezetimibe-glucuronide

Base Information

• Chemical Name: Ezetimibe-glucuronide
• CAS No.: 190448-57-8
• Molecular Formula: C₃₀H₂₉F₂NO₉
• Molecular Weight: 585.558
• Hs Code.: 29389090
• UNII: V7FA38E13K
• DSSTox Substance ID: DTXSID10432454
• Nikkaji Number: J1.010.095J
• Pharos Ligand ID: L4GFKWVAZLAC
• ChEMBL ID: CHEMBL321017
• Mol file: 190448-57-8.mol

Synonyms:ezetimibe glucuronide

Chemical Property of Ezetimibe-glucuronide

Chemical Property:

• Melting Point: 140-150°C
• PSA: 156.99000
• LogP: 2.51870
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 585.18103783
• Heavy Atom Count: 42
• Complexity: 921

Purity/Quality:

98%Min ^*data from raw suppliers

Ezetimibe b-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)OC5C(C(C(C(O5)C(=O)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1[C@@H]2[C@H](C(=O)N2C3=CC=C(C=C3)F)CC[C@@H](C4=CC=C(C=C4)F)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O
• Uses: Phase-II metabolite of Ezetimibe, an antihyperlipoproteinemic. A Cholesterol absorption inhibitor. This compound is very hygroscopic. Handle with care Glucuronide metabolite of Ezetimibe Phase-II metabolite of Ezetimibe, an antihyperlipoproteinemic. A Cholesterol absorption inhibitor.This compound is very hygroscopic. Handle with care.

Technology Process of Ezetimibe-glucuronide

There total 5 articles about Ezetimibe-glucuronide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-3-[(S)-3-acetoxy-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester (190448-56-7) → [14C]-Ezetimibe glucuronide (190448-57-8)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 18h;

DOI:10.1002/anie.200460348

Reference yield:

(1S)-1-(4-fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]propyl acetate (190448-46-5,1044664-24-5) → [14C]-Ezetimibe glucuronide (190448-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / BF₃*OEt₂ / CH₂Cl₂ / -20 - 20 °C

2: 67 percent / Et₃N / aq. methanol / 18 h / 20 °C

With boron trifluoride diethyl etherate; triethylamine; In methanol; dichloromethane;

DOI:10.1002/anie.200460348

Reference yield:

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3) → [14C]-Ezetimibe glucuronide (190448-57-8)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrazine acetate / dimethylformamide / 20 h / 55 °C

2: Cs₂CO₃ / CH₂Cl₂ / 3 h

3: 52 percent / BF₃*OEt₂ / CH₂Cl₂ / -20 - 20 °C

4: 67 percent / Et₃N / aq. methanol / 18 h / 20 °C

With boron trifluoride diethyl etherate; hydrazinium monoacetate; caesium carbonate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200460348

upstream raw materials:

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-3-[(S)-3-acetoxy-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

Refernces

• 1、 Vacarro, Wayne D.,Davis, Harry R.. "Sugar-Substituted 2-Azetidinone Cholesterol Absorption Inhibitors: Enhanced Potency by Modification of the Sugar". . p. 313 - 318. Retrieved 2007/10/03.